$2,199,000

A rare turnkey Shelter Island retreat with two distinct homes tucked away on nearly an acre in the heart of Shelter Island, 64A North Midway Road presents a truly unique opportunity to own two homes on one private property. Surrounded by mature trees, expansive lawns, and a picturesque pond next… Read More door, this exceptional estate blends privacy, flexibility, and timeless charm. This rare property offers remarkable versatility to fit your lifestyle. The welcoming ranch-style main home offers a comfortable living space with 3 bedrooms and two full bathrooms. A spacious kitchen with abundant cabinetry flows seamlessly into the dining area, creating an inviting setting for everyday living and entertaining. The living room, anchored by a wood-burning fireplace, provides a warm and cozy gathering place throughout the seasons. Step outside to the expansive rear deck, complete with a hot tub overlooking a large, private backyard with room for a pool, an ideal setting for entertaining, relaxing, or enjoying peaceful evenings. A welcoming front porch, an attached one-car garage, and a carport. Privately positioned toward the rear of the property, the stunning barn-style home feels like a secluded retreat. Overlooking a tranquil pond, this approx. The residence is filled with warmth, character, and natural light. The dramatic main room features soaring vaulted ceilings with exposed beams, a gas fireplace, and an impressive wall of windows that captures beautiful views while flooding the home with sunshine. French doors that open onto an expansive 500 square foot mahogany deck with built-in storage, creating the perfect place to enjoy morning coffee, outdoor dining, or simply unwind. The barn home also features two spacious bedrooms, two full bathrooms, a large loft, and a well-appointed kitchen. The oversized lower-level garage offers exceptional storage for vehicles, recreational equipment, bicycles, tools, and more, while additional facilities and energy-efficient solar panels further enhance the home’s appeal. The beautifully landscaped .95 acre property provides an uncommon sense of privacy while remaining just minutes from the Shelter Island beaches, marinas, restaurants, shops, farm stands, and nature preserve. 64A North Midway Road offers possibilities that are rarely available on Shelter Island. Read Less

Listing Courtesy of Douglas Elliman Real Estate.

Listing Snapshot

Days Online

Last Updated

Sep 2, 2026

Property Type

Single Family Residence

Beds

Full Baths

Square Ft.

2,642

Year Built

1977

Property Tax

$7,216

MLS Number

1029569

30 Days Snapshot Of 11964

$1.46M

+28%

(avg) sold price

home sold

367

+252%

(avg) days on market

Snapshot

Area Map

Additional Details

Appliances & Equipment

Description: Convection Oven, Dishwasher, Dryer, Electric Cooktop, Electric Range, Electric Water Heater, Exhaust Fan, Freezer, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer, Tankless Water Heater

Basement

Description: Bilco Door(s), Full

Building

Area: 2642, Architecture: Barndominium, Ranch, Construction Materials: Batts Insulation, Cedar, Frame, HardiPlank Type, Year Built: 1977

Cooling

Details: Central Air

Floors

Flooring: Ceramic Tile, Combination, Hardwood

Garage

Garage Spaces: 3

Heating

Heating: Ducts, Forced Air, Hot Water, Oil

Lot

Acres: 1

Parking

Carport Spaces: 1

Utilities

Sewer: Septic Tank, Water Source: Well, Utilities: Electricity Connected, Phone Connected, Propane, Water Connected

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